Don’t plan in too many 1 night stints, unless you’re tight for time. In my opinion, it’s better to visit less places so you can actually fully see that place then try to fit in too many stops.
Have a plan, but leave room for spontaneity. Booking into too much will leave you tired and overwhelmed.
Never leave yourself with too little gas. On some stretches of road the rest stops are few and far between.
Have your vehicle checked beforehand.
Have all car documents with you.
Get directions: mapquest directions map

Stop 1. New York City (3-4 nights)

New York City is a great place to start your adventure. It is where my family is from and where I now reside. This will be the most expensive stop on your tour, but it will also be one of the most intriguing and diverse!

You don't need a car in New York, so wait until you're on your way out before renting one.

You should try Pizza (Artichoke, Prince St., Joe's), Bagels (Ess-a-bagel, Russ+Daughters), Burgers (Emmy Squared, Raoul's, Shake Shack), and Pastrami (Katz Deli) while in NYC.

I've put together a simple itinerary for you below, but you can also read my complete guide to 4 days in New York.

Stop 2. Montauk, NY (2 nights)

Montauk is located on Long Island's South Fork and is known as "The End." It's in the Hamptons, at the very tip of Long Island's peninsula. Long Island is located east of New York City and is essentially an extension of the same geographical mass that Queens and Brooklyn sit on.

Montauk is an old surfing and fishing hamlet that has become trendy due to the influx of New Yorkers during the summer months. It's a great location to unwind after a hectic few days in NYC while yet maintaining that vibrant attitude.

Stop 3. Asbury Park, NJ (2 nights) 

Asbury Park is a quirky, retro coastal town with a great boardwalk and a lengthy musical history. It's a well-known hangout for rock & roll musicians, artists, and surfers.

Stop 4. Rehoboth Beach, Delaware (2 nights)

Rehoboth Beach has long been a popular vacation spot for tourists visiting from Washington, D.C. The throwback seaside town today attracts visitors from all over the country, mainly from Baltimore, Philadelphia, New York City, and Washington, D.C.

Stop 5. Norfolk/Virginia Beach (1 night)

Norfolk is a naval hub and is south of the Chesapeake Bay. It just so happens to be the biggest naval base in the world and the home of NATO's North American headquarters.

Norfolk and Virginia Beach are only 20 minutes apart by car, so it's easy to see both. Even though I didn't like Virginia Beach that much, there were a few good places to visit.

Stop 6. Blue Ridge Parkway/Asheville (3 nights)

Asheville is a cool, hippie-style city in the North Carolina Mountains. It is between the Blue Ridge Mountains and the Smokey Mountains, which are only 70 miles away.

Stop 7. Hilton Head, South Carolina (2 nights)

Hilton Head is a popular place to visit on the East Coast. Many people like to bike around the resort town, which is 12 miles long and 5 miles wide. Many people who come here on vacation rent big houses on the beach, but there are other options. We stayed at the Palerma Inn and Suites, which at the time was pretty cheap.

Stop 8. Charleston, SC (3 nights)

One of the most popular cities in the U.S. right now is Charleston. It gets a lot of attention for its old downtown with cobblestone streets, its lively food scene, and the beautiful beaches close by.

Stop 9. The Florida Keys

There were many aspects of Key West and the other Keys that I adored. Aside from the obvious; azure water, excellent seafood, and magnificent resorts, it just has that vibe!